DE2644121A1 - Neue pyridobenzodiazepinone, verfahren zu ihrer herstellung und diese enthaltende arzneimittel - Google Patents
Neue pyridobenzodiazepinone, verfahren zu ihrer herstellung und diese enthaltende arzneimittelInfo
- Publication number
- DE2644121A1 DE2644121A1 DE19762644121 DE2644121A DE2644121A1 DE 2644121 A1 DE2644121 A1 DE 2644121A1 DE 19762644121 DE19762644121 DE 19762644121 DE 2644121 A DE2644121 A DE 2644121A DE 2644121 A1 DE2644121 A1 DE 2644121A1
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- group
- dihydro
- pyrido
- carbon atoms
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- MGDDXKBVXQCWER-UHFFFAOYSA-N pyrido[2,3-i][1,2]benzodiazepin-3-one Chemical compound N1=NC(=O)C=CC2=CC=C(N=CC=C3)C3=C21 MGDDXKBVXQCWER-UHFFFAOYSA-N 0.000 title claims description 18
- 238000000034 method Methods 0.000 title claims description 16
- 238000004519 manufacturing process Methods 0.000 title claims description 12
- 229940126601 medicinal product Drugs 0.000 title claims 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 112
- -1 methylpiperazino group Chemical group 0.000 claims description 50
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 27
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 26
- 239000012312 sodium hydride Substances 0.000 claims description 26
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 26
- 150000001875 compounds Chemical class 0.000 claims description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
- 150000007524 organic acids Chemical class 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 150000007522 mineralic acids Chemical class 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 7
- 235000005985 organic acids Nutrition 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 239000012442 inert solvent Substances 0.000 claims description 6
- 239000008096 xylene Substances 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 4
- 238000003776 cleavage reaction Methods 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 230000007017 scission Effects 0.000 claims description 4
- 150000001447 alkali salts Chemical class 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 claims description 3
- 229910000103 lithium hydride Inorganic materials 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 claims description 3
- 229910000105 potassium hydride Inorganic materials 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 150000001340 alkali metals Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 claims description 2
- UTTXEYODTTZTMS-UHFFFAOYSA-N 1-piperidin-1-yl-2-pyrrolidin-1-ylazepane Chemical compound C1CCCN1C1N(N2CCCCC2)CCCCC1 UTTXEYODTTZTMS-UHFFFAOYSA-N 0.000 claims 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 2
- 239000000969 carrier Substances 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- 239000000243 solution Substances 0.000 description 30
- 238000002844 melting Methods 0.000 description 29
- 230000008018 melting Effects 0.000 description 29
- 239000000203 mixture Substances 0.000 description 29
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
- 239000002480 mineral oil Substances 0.000 description 22
- 235000010446 mineral oil Nutrition 0.000 description 22
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 239000003921 oil Substances 0.000 description 16
- HCDXLUKTYFLIEM-UHFFFAOYSA-N 1,2-benzodiazepin-5-one Chemical compound O=C1C=CN=NC2=CC=CC=C12 HCDXLUKTYFLIEM-UHFFFAOYSA-N 0.000 description 15
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 13
- 229910052938 sodium sulfate Inorganic materials 0.000 description 13
- 235000011152 sodium sulphate Nutrition 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000004480 active ingredient Substances 0.000 description 9
- 238000009835 boiling Methods 0.000 description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 229920002261 Corn starch Polymers 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 239000008120 corn starch Substances 0.000 description 7
- 229940099112 cornstarch Drugs 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 6
- WVUULNDRFBHTFG-UHFFFAOYSA-N 3-chloro-n,n-diethylpropan-1-amine Chemical compound CCN(CC)CCCCl WVUULNDRFBHTFG-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 229910021529 ammonia Inorganic materials 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 239000000829 suppository Substances 0.000 description 6
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 239000013543 active substance Substances 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
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- 235000011389 fruit/vegetable juice Nutrition 0.000 description 5
- 229920000159 gelatin Polymers 0.000 description 5
- 235000019322 gelatine Nutrition 0.000 description 5
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 5
- 235000019359 magnesium stearate Nutrition 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 238000006114 decarboxylation reaction Methods 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 4
- 239000008298 dragée Substances 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- CPJSUEIXXCENMM-UHFFFAOYSA-N phenacetin Chemical compound CCOC1=CC=C(NC(C)=O)C=C1 CPJSUEIXXCENMM-UHFFFAOYSA-N 0.000 description 4
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- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 4
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 4
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- 230000007059 acute toxicity Effects 0.000 description 3
- 231100000403 acute toxicity Toxicity 0.000 description 3
- GLZXFITXXAMCRJ-UHFFFAOYSA-N azepin-4-one Chemical compound O=C1C=CC=NC=C1 GLZXFITXXAMCRJ-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- ZGLDQGIONSGJCN-UHFFFAOYSA-N diazepin-5-one Chemical compound O=C1C=CN=NC=C1 ZGLDQGIONSGJCN-UHFFFAOYSA-N 0.000 description 3
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- YMDNODNLFSHHCV-UHFFFAOYSA-N 2-chloro-n,n-diethylethanamine Chemical compound CCN(CC)CCCl YMDNODNLFSHHCV-UHFFFAOYSA-N 0.000 description 1
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- 229910002016 Aerosil® 200 Inorganic materials 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 206010022998 Irritability Diseases 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 238000011785 NMRI mouse Methods 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 241000906446 Theraps Species 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 230000001088 anti-asthma Effects 0.000 description 1
- 239000000924 antiasthmatic agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 235000019568 aromas Nutrition 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 235000013871 bee wax Nutrition 0.000 description 1
- 239000012166 beeswax Substances 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 230000000572 bronchospasmolytic effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 230000003419 expectorant effect Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 208000030603 inherited susceptibility to asthma Diseases 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- GTNGRRLCBNNJHB-UHFFFAOYSA-N n-benzyl-3-chloro-n-ethylpropan-1-amine Chemical compound ClCCCN(CC)CC1=CC=CC=C1 GTNGRRLCBNNJHB-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 235000020030 perry Nutrition 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/10—Expectorants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (38)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762644121 DE2644121A1 (de) | 1976-09-30 | 1976-09-30 | Neue pyridobenzodiazepinone, verfahren zu ihrer herstellung und diese enthaltende arzneimittel |
| AT622077A AT355580B (de) | 1976-09-30 | 1977-08-29 | Verfahren zur herstellung neuer pyridobenzo- diazepinone und ihrer salze |
| FI772772A FI62086C (fi) | 1976-09-30 | 1977-09-20 | Foerfarande foer framstaellning av bronkosekreterolytiska 5,11-dihydro-5h-pyrido(2,3-b)(1,5)bensodiazepin-5-oner |
| BG037376A BG28066A3 (bg) | 1976-09-30 | 1977-09-20 | Метод за получаване на пиридобензодиазепинони |
| AU29038/77A AU512831B2 (en) | 1976-09-30 | 1977-09-22 | 2-methyl-5hpyrido [2,3-b] [benzodiazpine-5-one derivatives |
| DD77201205A DD134351A5 (de) | 1976-09-30 | 1977-09-26 | Verfahren zur herstellung neuer pyridobenzodiazepinonen |
| CH1180077A CH637955A5 (de) | 1976-09-30 | 1977-09-27 | Verfahren zur herstellung neuer pyridobenzodiazepinone und ihrer salze. |
| SU772524544A SU786900A3 (ru) | 1976-09-30 | 1977-09-27 | Способ получени пиридобензодиазепинонов или их солей |
| CS776253A CS196388B2 (en) | 1976-09-30 | 1977-09-27 | Method of producing novel pyridobenzodiazepinones |
| LU78192A LU78192A1 (enrdf_load_stackoverflow) | 1976-09-30 | 1977-09-28 | |
| DK428377A DK143752C (da) | 1976-09-30 | 1977-09-28 | Analogifremgangsmaade til fremstilling af pyridobenzodiazepinoner eller farmakologisk acceptable salte deraf |
| HU77TO1063A HU179802B (en) | 1976-09-30 | 1977-09-28 | Process for producing new pyrido-square bracket-2,3,b-square bracket closed-square bracket-1,5-square bracket closed-benzodlasepin-5-one derivatives |
| US05/837,578 US4167570A (en) | 1976-09-30 | 1977-09-28 | 2-Methyl-6-alkyl-11-aminoalkyl-6,11-dihydro-5H-pyrido(2,3-B)(1,5)benzodiazepin-5-ones and salts thereof |
| CA287,654A CA1084049A (en) | 1976-09-30 | 1977-09-28 | Pyridobenzodiazepinones, processes for their preparation and pharmaceuticals containing them |
| YU02312/77A YU231277A (en) | 1976-09-30 | 1977-09-28 | Process for preparing new pyrido-benzodiazepine |
| ZA00775816A ZA775816B (en) | 1976-09-30 | 1977-09-29 | Improvements relating to pyridobenzodiazepinones |
| IL53026A IL53026A (en) | 1976-09-30 | 1977-09-29 | 6-alkyl-11-(cyclic)aminoalkyl-2-methyl-6,11-dihydro-5h-pyrido(2,3-b)(1,5)-benzodiazepin-5-ones,their preparation andpharmaceutical compositions containing them |
| GR54460A GR64050B (en) | 1976-09-30 | 1977-09-29 | Method for the preparation of new pyridobezodiazepinones |
| NL7710646A NL7710646A (nl) | 1976-09-30 | 1977-09-29 | Nieuwe pyridobenzodiazepinonen, werkwijze ter bereiding daarvan en van deze nieuwe verbin- dingen bevattende preparaten. |
| GB40555/77A GB1538366A (en) | 1976-09-30 | 1977-09-29 | Pyridobenzodiazepines |
| NZ185302A NZ185302A (en) | 1976-09-30 | 1977-09-29 | 2-methyl-6-alkyl-11-(-substituted aminoalkyl)-6,11-dihydro-5h-pyrido (2,3-b) (1,5) benzodiazepin-5-ones |
| IE1994/77A IE45702B1 (en) | 1976-09-30 | 1977-09-29 | New pyridobenzodiazepinones, processes for their preparation and pharmaceutical compositions containing them |
| PH20285A PH14714A (en) | 1976-09-30 | 1977-09-29 | 2-methyl-6-alkyl-11-aminoalkyl-6,11,-dihydro-5h-pyrido(2,3-b)(1,5)benzodiazepin-5-ones and salts thereof |
| NO773344A NO146776C (no) | 1976-09-30 | 1977-09-29 | Analogifremgangsmaate for fremstilling av fysiologisk aktive pyridobenzodiazepiner |
| ES462746A ES462746A1 (es) | 1976-09-30 | 1977-09-29 | Procedimiento para la preparacion de nuevas piridobenzodia- zepinas. |
| PL1977201133A PL104866B1 (pl) | 1976-09-30 | 1977-09-29 | Sposob wytwarzania nowych pirydobenzodwuazepinonow |
| BE181322A BE859213A (fr) | 1976-09-30 | 1977-09-29 | Pyridobenzodiazepinones, leur preparation et leurs utilisations therapeutiques |
| JP11730977A JPS5344595A (en) | 1976-09-30 | 1977-09-29 | Pyridbenzodiazepine |
| PT67097A PT67097B (de) | 1976-09-30 | 1977-09-29 | Neue pyridobenzodiazepinone verfahren zu ihrer herstellungund diese enthaltende arzneimittel |
| SE7710993A SE425740B (sv) | 1976-09-30 | 1977-09-30 | Analogiforfarande for framstellning av pyrido(2,3-b)(1,5)benso-diazepiner |
| FR7729530A FR2372164A1 (fr) | 1976-09-30 | 1977-09-30 | Pyridobenzodiazepinones, leur preparation et leurs utilisations therapeutiques |
| ES468585A ES468585A1 (es) | 1976-09-30 | 1978-04-06 | Procedimiento para la preparacion de nuevas piridobenzodia- zepinonas. |
| ES468586A ES468586A1 (es) | 1976-09-30 | 1978-04-06 | Procedimiento para la preparacion de nuevas piridobenzodia- zepinonas. |
| SU782624299A SU722486A3 (ru) | 1976-09-30 | 1978-06-09 | Способ получени пиридобензодиазепинонов или их солей |
| AT269779A AT355582B (de) | 1976-09-30 | 1979-04-11 | Verfahren zur herstellung neuer pyridobenzo- diazepinone und ihrer salze |
| AT269379A AT355581B (de) | 1976-09-30 | 1979-04-11 | Verfahren zur herstellung neuer pyrido- benzodiazepinone und ihrer salze |
| CH298682A CH637957A5 (de) | 1976-09-30 | 1982-05-13 | Verfahren zur herstellung neuer pyridobenzodiazepinone und ihrer salze. |
| CH298782A CH637958A5 (de) | 1976-09-30 | 1982-05-13 | Verfahren zur herstellung neuer pyridobenzodiazepinone und ihrer salze. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762644121 DE2644121A1 (de) | 1976-09-30 | 1976-09-30 | Neue pyridobenzodiazepinone, verfahren zu ihrer herstellung und diese enthaltende arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2644121A1 true DE2644121A1 (de) | 1978-04-06 |
Family
ID=5989298
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762644121 Withdrawn DE2644121A1 (de) | 1976-09-30 | 1976-09-30 | Neue pyridobenzodiazepinone, verfahren zu ihrer herstellung und diese enthaltende arzneimittel |
Country Status (31)
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0085893A3 (en) * | 1982-02-09 | 1984-03-21 | Dr. Karl Thomae Gmbh | Pyridobenzodiazepinones, process for their preparation and pharmaceutical compositions containing them |
| FR2850654A1 (fr) * | 2003-02-03 | 2004-08-06 | Servier Lab | Nouveaux derives d'azepines tricycliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5695597U (enrdf_load_stackoverflow) * | 1979-12-18 | 1981-07-29 | ||
| US4749788A (en) * | 1987-04-13 | 1988-06-07 | A. H. Robins Company, Incorporated | Process for the preparation of aryl-pyrido(1,4) benzodiazepines |
| ATE161535T1 (de) * | 1989-04-20 | 1998-01-15 | Boehringer Ingelheim Pharma | 6,11-dihydro-5h-pyrido(2,3-b)(1,5)benzodiazepin 5-one und thione und ihre verwendung für die vorbeugung oder behandlung von aids |
| US6048857A (en) * | 1989-10-17 | 2000-04-11 | Ellinwood, Jr.; Everett H. | Dosing method of administering medicaments via inhalation administration |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2424811C3 (de) * | 1974-05-22 | 1981-08-20 | Dr. Karl Thomae Gmbh, 7950 Biberach | Pyrido-benzodiazepinone, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel |
| PL60440Y1 (en) * | 1999-01-26 | 2004-05-31 | Pil I Narzedzi Wapienica Sa Fa | Double-sided hacksaw blade |
| PL60439Y1 (en) * | 1999-09-03 | 2004-05-31 | Zdt Komag Sp Z Oo | Regenerated scraper of a chain-type scraper conveyor |
-
1976
- 1976-09-30 DE DE19762644121 patent/DE2644121A1/de not_active Withdrawn
-
1977
- 1977-08-29 AT AT622077A patent/AT355580B/de active
- 1977-09-20 FI FI772772A patent/FI62086C/fi not_active IP Right Cessation
- 1977-09-20 BG BG037376A patent/BG28066A3/xx unknown
- 1977-09-22 AU AU29038/77A patent/AU512831B2/en not_active Expired
- 1977-09-26 DD DD77201205A patent/DD134351A5/xx unknown
- 1977-09-27 CS CS776253A patent/CS196388B2/cs unknown
- 1977-09-27 SU SU772524544A patent/SU786900A3/ru active
- 1977-09-27 CH CH1180077A patent/CH637955A5/de not_active IP Right Cessation
- 1977-09-28 CA CA287,654A patent/CA1084049A/en not_active Expired
- 1977-09-28 YU YU02312/77A patent/YU231277A/xx unknown
- 1977-09-28 DK DK428377A patent/DK143752C/da not_active IP Right Cessation
- 1977-09-28 LU LU78192A patent/LU78192A1/xx unknown
- 1977-09-28 US US05/837,578 patent/US4167570A/en not_active Expired - Lifetime
- 1977-09-28 HU HU77TO1063A patent/HU179802B/hu unknown
- 1977-09-29 PH PH20285A patent/PH14714A/en unknown
- 1977-09-29 NZ NZ185302A patent/NZ185302A/xx unknown
- 1977-09-29 BE BE181322A patent/BE859213A/xx unknown
- 1977-09-29 PL PL1977201133A patent/PL104866B1/xx unknown
- 1977-09-29 JP JP11730977A patent/JPS5344595A/ja active Pending
- 1977-09-29 ES ES462746A patent/ES462746A1/es not_active Expired
- 1977-09-29 GR GR54460A patent/GR64050B/el unknown
- 1977-09-29 NO NO773344A patent/NO146776C/no unknown
- 1977-09-29 NL NL7710646A patent/NL7710646A/xx not_active Application Discontinuation
- 1977-09-29 GB GB40555/77A patent/GB1538366A/en not_active Expired
- 1977-09-29 PT PT67097A patent/PT67097B/pt unknown
- 1977-09-29 IE IE1994/77A patent/IE45702B1/en unknown
- 1977-09-29 ZA ZA00775816A patent/ZA775816B/xx unknown
- 1977-09-29 IL IL53026A patent/IL53026A/xx unknown
- 1977-09-30 SE SE7710993A patent/SE425740B/xx unknown
- 1977-09-30 FR FR7729530A patent/FR2372164A1/fr active Granted
-
1978
- 1978-04-06 ES ES468585A patent/ES468585A1/es not_active Expired
- 1978-04-06 ES ES468586A patent/ES468586A1/es not_active Expired
- 1978-06-09 SU SU782624299A patent/SU722486A3/ru active
-
1982
- 1982-05-13 CH CH298682A patent/CH637957A5/de not_active IP Right Cessation
- 1982-05-13 CH CH298782A patent/CH637958A5/de not_active IP Right Cessation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0085893A3 (en) * | 1982-02-09 | 1984-03-21 | Dr. Karl Thomae Gmbh | Pyridobenzodiazepinones, process for their preparation and pharmaceutical compositions containing them |
| FR2850654A1 (fr) * | 2003-02-03 | 2004-08-06 | Servier Lab | Nouveaux derives d'azepines tricycliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
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